A one-pot reduction-transimition-reduction synthesis of N-substituted β-ethanolamines from cyanohydrins

Article abstract of DOI:10.1016/S0040-4020(01)88477-5

An efficient (74% - 97% yield) three-step one-pot synthesis of (R)-Halostachine and analogues from O-protected optically active cyanohydrins is described. The reaction sequence involves a DIBAL reduction of the nitrile to an imine, transimination to a secondary imine and sodium borohydride reduction to the corresponding N-substituted β-ethanolamine. Both O-protected as well as unprotected reaction products can be obtained.